(Z)-5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)imidazolidine-2,4-dione | 1256244-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (Z)-5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)imidazolidine-2,4-dione
• 英文别名: (5Z)-5-(1H-pyrrolo[2,3-b]pyridin-3-ylmethylidene)imidazolidine-2,4-dione
• CAS: 1256244-69-5
• 化学式: C₁₁H₈N₄O₂
• 分子量: 228.21
• InChiKey: NUTGDFQXTBGPLK-YWEYNIOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  86.88
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  海因 、 7-氮杂吲哚-3-甲醛 在 碳酸氢钠 、 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 以59.2%的产率得到(Z)-5-((1H-pyrrolo[2,3-b]pyridin-3-yl)methylene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis

  摘要：

  Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. In the process of discovery of new antiproliferative and anti-metastatic agents against prostate cancer, marine-derived phenylmethylene hydantoin (PMH) derivatives were identified with activity level range between 50 and 200 mu M. 3D-QSAR CoMFA model was used in virtual screening of commercially available derivatives of PMH. PMH derivatives with manifold increase in anti-migratory and anti-invasive activities were discovered using wound-healing and Cultrex invasion assays. Benzene ring replacement with other heterocyclic rings did not significantly improve the methylene hydantoins activities. Multivariate analysis performed on the whole series of methylene hydantoins, which further supported the findings of CoMFA model. Predictive QSAR model with conventional r(2) and cross-validated coefficient (q(2)) values up to 0.982 and 0.803 were established. The molecular volume (MV) and the log P were identified as critical parameters for methylene hydatoins migration inhibitory activity. PMH is a novel anti-metastatic lead class with potential therapeutic activity against prostate cancer. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.066

文献信息

• PYRROLIDINE DERIVATIVE, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING BETA-AMYLOID OR TAU PROTEIN-ASSOCIATED DISEASES CONTAINING SAME
  申请人：Yonsei University, University-Industry Foundation(UIF).

  公开号：EP4083037A1

  公开（公告）日：2022-11-02

  Provided are: a novel pyrrolidine derivative or a pharmaceutically acceptable salt thereof; and a pharmaceutical composition containing same and having the effects of inhibiting beta-amyloid and/or tau protein aggregation, and/or breaking down beta-amyloid and/or tau protein aggregates, and/or preventing and/or treating beta-amyloid and/or tau protein-associated diseases.

  本文提供了：一种新型吡咯烷衍生物或其药学上可接受的盐；以及一种含有该衍生物并具有抑制β-淀粉样蛋白和/或tau蛋白聚集和/或分解β-淀粉样蛋白和/或tau蛋白聚集和/或预防和/或治疗β-淀粉样蛋白和/或tau蛋白相关疾病的作用的药物组合物。
• [EN] PYRROLIDINE DERIVATIVE, AND PHARMACEUTICAL COMPOSITION FOR PREVENTING OR TREATING BETA-AMYLOID OR TAU PROTEIN-ASSOCIATED DISEASES CONTAINING SAME<br/>[FR] DÉRIVÉ DE PYRROLIDINE ET COMPOSITION PHARMACEUTIQUE DE PRÉVENTION OU DE TRAITEMENT DE MALADIES ASSOCIÉES À LA PROTÉINE BÊTA-AMYLOÏDE OU TAU CONTENANT CE DERNIER<br/>[KO] 피롤리딘 유도체 및 이를 포함하는 베타-아밀로이드 또는 타우 단백질 관련 질병의 예방 또는 치료용 약학 조성물
  申请人：YONSEI UNIV UNIV INDUSTRY FOUNDATION UIF

  公开号：WO2021133037A1

  公开（公告）日：2021-07-01

  신규한 피롤리딘 유도체 또는 이의 약학적으로 허용 가능한 염, 및 이를 포함하는 베타-아밀로이드 및/또는 타우 단백질의 응집 억제 및/또는 베타-아밀로이드 및/또는 타우 단백질의 응집체 분해, 및/또는 베타-아밀로이드 및/또는 타우 단백질 관련 질병의 예방 및/또는 치료 효과를 갖는 약학 조성물이 제공된다.
• Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis
  作者：Mohammad A. Khanfar、Khalid A. El Sayed

  DOI：10.1016/j.ejmech.2010.08.066

  日期：2010.11

  Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. In the process of discovery of new antiproliferative and anti-metastatic agents against prostate cancer, marine-derived phenylmethylene hydantoin (PMH) derivatives were identified with activity level range between 50 and 200 mu M. 3D-QSAR CoMFA model was used in virtual screening of commercially available derivatives of PMH. PMH derivatives with manifold increase in anti-migratory and anti-invasive activities were discovered using wound-healing and Cultrex invasion assays. Benzene ring replacement with other heterocyclic rings did not significantly improve the methylene hydantoins activities. Multivariate analysis performed on the whole series of methylene hydantoins, which further supported the findings of CoMFA model. Predictive QSAR model with conventional r(2) and cross-validated coefficient (q(2)) values up to 0.982 and 0.803 were established. The molecular volume (MV) and the log P were identified as critical parameters for methylene hydatoins migration inhibitory activity. PMH is a novel anti-metastatic lead class with potential therapeutic activity against prostate cancer. (C) 2010 Elsevier Masson SAS. All rights reserved.